The document that establishes the birth of the original aggregate of Pontelandolfo dates back to 980; it is an act of donation of the territory of Ponte S. Anastasia by the Beneventan prince Pandolfo Capodiferro and his son Landolfo, to the Benedictine monks of Montecassino.

Tradition has it that the monks themselves were interested in the construction of both the castle and the church of SS. Annunziata.

A different interpretation, motivated by the discovery of the coat of arms kept in the mother church of SS. Salvatore, wants that the Lombard prince "Landolfo", about a kilometer from the ancient Casale di Santa Teodora of the locality Sorgenza, in order to cross the stream Alente built a bridge, to which he gave his name: from this Pontem Landulphi (then Pontelandolfo) the name, evoked for the first time in 1138 in the chronicle of the medieval writer Falcone, to indicate the town that would have formed nearby. It may well be that in that same site in Samnite antiquity there was one of the Samnite Oppids, on the Numician way, communicating the Caudins with the Pentris.

Several events, in the centuries that followed, devastated the village.
The first known event dates back to 1138 when Pontelandolfo suffered a first siege and fire at the hands of King Roger the Norman, due to the rebellion of the Count of Ariano. So it’s clear that it was located in the County of Ariano, which was abolished by the Norman Kings.

It was a fief of the Bursello, the Sanframondo, the Svevi, the Angiò, as well as the Gambatesa who for defensive reasons, to protect the small village, already surrounded entirely by walls, built an imposing crenellated tower, still existing in all its original majesty, eternal symbol of the country.
In 1349 a strong earthquake completely destroyed the town.

Rebuilt, it was again destroyed almost entirely by a strong earthquake in 1456.
In 1461 it suffered a further siege and fire this time by Ferdinand I of Aragon in war against John of Anjou and his vassals.
Later, Pontelandolfo, with its land, was sold by Ferdinand II of Aragon to Andrea di Capua.

Finally, after further vicissitudes, it became in 1466 the land of the Carafa until 1806, when feudalism was abolished, which here too made its burden felt, demanding expensive payments from the shepherds who led the herds into the mountains.
In 1688 once again a violent earthquake severely damaged the town of Pontelandolfo decimating much of the population already hard hit a few years before the plague.
In 1806 Joseph Napoleon, with the abolition of slavery, put an end to the centuries-old quarrels.

Only with the advent of the eighteenth century, began to emerge in a concrete way a demographic awakening, encouraged by the stability guaranteed by the new Bourbon state, which took shape especially during the nineteenth century.
It is from this period that the arts and crafts linked to local resources have become established. Pastoralism undergoes a significant increase with the consequent production of textile and embroidery works, iron, wood and stone, which will represent the economy and activity of the country.

Before the construction of the Benevento-Campobasso railway, located on the Sannitica road, Pontelandolfo was an important centre of transit and trade between Naples and Sannio, with a rich grain customs established in 1853 by decree of Ferdinand II of Bourbon.
Several times over the centuries the object of natural disasters and not, Pontelandolfo lives yet another drama during the well-known blood events of the summer of 1861, thus paying with death and destruction the much-coveted Unification of Italy.

The vicious crimes committed on August 14, 1861, have undoubtedly marked the saddest page in the long history of this country.
It was the year 1861, while the Italian upheavals prepared for the new kingdom, a band of brigands commanded by Cosimo Giordano arrived on August 7 in Pontelandolfo looting the houses of the citizens who had meanwhile fled, and killing a shopkeeper and another peaceful citizen. On August 11 to quell the riots was sent from Campobasso a squad of 45 soldiers of the 36 Second Line. with Lieutenant Bracci and 4 carabinieri. These attacked took refuge in the tower, but provoked by the insurgents and ran out of ammunition, they attempted a sortie heading towards Casalduni. Here a large band of brigands, led by Angelo Pica made them up.
So it was that at dawn on 14 August by order of General Cialdini a battalion of 500 bersaglieri commanded by Lieutenant Pier Eleonoro Negri reached the country.
The people, unaware of what had happened in Casalduni, fled from the village.

But the order was carried out. The next day a dispatch announced laconically in the official newspapers "yesterday morning at dawn justice was done against Pontelandolfo ...".